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I think the Madonna-Ayu comparison works. They're both famous for their changing styles. Both had determination: their voices weren't the best but they overcame that with hard work and charisma. They've always been able to have some control over their careers: Madonna is a good businesswoman and Ayu write her own lyrics right from the start. Ayu's career isn't as iconic as Madonna's but being around since '98 and still getting #1s is a respectable accomplishment.
I'd guess that Britney is most famous for her sexiness and dancing, two things that were never a huge part of Ayu's image. She's also come across as depending on other people to tell her what to do (managers, producers, her mother), unlike Ayu who doesn't seem to be lost when she's being interviewed. Britney has also had two very public relationships while Ayu keeps silent about her love life. She also hasn't released a studio album since '03 but Ayu keeps on working and touring. Those are some of the main reasons why I don't like the Britney-Ayu comparison: they don't have much in common except level of fame and calling Ayu a Britney-type would imply that her music/image are similar.
So when I call Ayu the Madonna of Japan I think the listener gets a decent enough idea of what her image/songs might be like, but if I called her the Britney of Japan I think there would be too much emphasis on sexiness and tabloid attention.
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